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Sailboat boats for sale in Florida

There are 104 new and used boats for sale in Florida. Find boats of all types and price ranges on BoatCrazy.com. We offer boats for sale by owner and dealers. Browse through Fishing Boats, Center Consoles, Pontoons, Cruisers, PWCs and more in Florida.
104 boats found within 200 miles out of 8,147 Boats Found

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  • 1988 Catalina 30

    1988 Catalina 30

    $24,900
    Hudson, FL
    • Hudson, FL
    • Sailboat
    • 30' / 10'
    • 1988 / Used
    • $24,900

    The 1988 Catalina 30 is a classic cruising sailboat that has long been appreciated for its combination of performance, comfort, and affordability. With a length overall (LOA) of 30... View Details

    View 24 Photos and Details Contact Seller
    $24,900
    VIEW DETAILS
  • 1984 Pearson 33

    1984 Pearson 33

    $24,750
    Jacksonville, FL
    • Jacksonville, FL
    • Sailboat
    • 33' / 0'
    • 1984 / Used
    • $24,750

    - Stock #219902 - Great condition, turn key, Large salon with expanding table. One head with sink and shower. Navigation station and more! If you are in the market for a sloop,... View Details

    View 10 Photos and Details Contact Seller
    $24,750
    VIEW DETAILS
  • 1991 Catalina 28

    1991 Catalina 28

    $23,499
    Cape Coral, FL
    • Cape Coral, FL
    • Sailboat
    • 28' / 0'
    • 1991 / Used
    • $23,499

    - Stock #214659 - What a GREAT Live aboard! Owner including a lot of nice upgrades! If you are in the market for a cruiser, look no further than this 1991 Catalina 28, just red... View Details

    View 10 Photos and Details Contact Seller
    $23,499
    VIEW DETAILS
  • 1975 Hallberg Rassy 35 Rasmus

    1975 Hallberg Rassy 35 Rasmus

    $23,000
    Key West, FL
    • Key West, FL
    • Sailboat
    • 35' / 0'
    • 1975 / Used
    • $23,000

    - Stock #215817 - In decent condition, full keel, fresh bottom/hull paint, new 3 bladed prop, must see! If you are in the market for a sloop, look no further than this 1975 Hal... View Details

    View 10 Photos and Details Contact Seller
    $23,000
    VIEW DETAILS
  • 1971 Gulfstar 36 Motorsailor TC

    1971 Gulfstar 36 Motorsailor TC

    $23,000
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 36' / 0'
    • 1971 / Used
    • $23,000

    - Stock #222682 - Great Liveaboard! Can be a Motorsailor or Trawler! If you are in the market for a motorsailer, look no further than this 1971 Gulfstar 36 Motorsailor TC, pric... View Details

    View 10 Photos and Details Contact Seller
    $23,000
    VIEW DETAILS
  • 1979 Irwin 34 Citation

    1979 Irwin 34 Citation

    $22,500
    Saint Petersburg, FL
    • Saint Petersburg, FL
    • Sailboat
    • 34' / 0'
    • 1979 / Used
    • $22,500

    - Stock #166217 - Beautiful and Luxurious, Great Condition, Live-aboard Ready, She will ply the Waters of your Dreams! If you are in the market for a sloop, look no further tha... View Details

    View 10 Photos and Details Contact Seller
    $22,500
    VIEW DETAILS
  • 1985 Kirie Elite 32

    1985 Kirie Elite 32

    $22,250
    Cape Coral, FL
    • Cape Coral, FL
    • Sailboat
    • 31' / 0'
    • 1985 / Used
    • $22,250

    - Stock #199827 - This European style Cruiser is beautiful inside and out with many upgrades, must see! If you are in the market for a cruiser, look no further than this 1985 K... View Details

    View 10 Photos and Details Contact Seller
    $22,250
    VIEW DETAILS
  • 1967 Columbia 38

    1967 Columbia 38

    $21,900
    Palmetto, FL
    • Palmetto, FL
    • Sailboat
    • 38' / 0'
    • 1967 / Used
    • $21,900

    - Stock #228043 - Classic lines by Charles Morgan. complete rebuild and repowered. Top speed 10 knots! If you are in the market for a cruiser, look no further than this 1967 Co... View Details

    View 10 Photos and Details Contact Seller
    $21,900
    VIEW DETAILS
  • 2003 Hunter 260

    2003 Hunter 260

    $21,595
    Saint Petersburg, FL
    • Saint Petersburg, FL
    • Sailboat
    • 26' / 0'
    • 2003 / Used
    • $21,595

    - Stock #193570 - Well maintained & sharp looking throughout, she is trailerable model 260 & she comes with many extras - the perfect family sailboat! If you are in the market... View Details

    View 10 Photos and Details Contact Seller
    $21,595
    VIEW DETAILS
  • 1985 Hunter 36

    1985 Hunter 36

    $21,500
    Stuart, FL
    • Stuart, FL
    • Sailboat
    • 36' / 0'
    • 1985 / Used
    • $21,500

    - Stock #167779 - Desireable tranferable slip. Boat has many upgrades, most of the hard work is done, add your touches and sail away. If you are in the market for a sloop, look... View Details

    View 10 Photos and Details Contact Seller
    $21,500
    VIEW DETAILS
  • 1988 Beneteau 285 WK

    1988 Beneteau 285 WK

    $20,750
    Miami, FL
    • Miami, FL
    • Sailboat
    • 28' / 0'
    • 1988 / Used
    • $20,750

    - Stock #232091 - Beautiful Beneteau in great condition, ready to sail. If you are in the market for a cruiser, look no further than this 1988 Beneteau 285 WK, priced right at... View Details

    View 9 Photos and Details Contact Seller
    $20,750
    VIEW DETAILS
  • 1993 Rhodes Rhodes 22

    1993 Rhodes Rhodes 22

    $20,650
    Seminole, FL
    • Seminole, FL
    • Sailboat
    • 22' / 0'
    • 1993 / Used
    • $20,650

    - Stock #213666 - Rhodes 22, Complete restoration of a great daysailing sailboat. Offers accepted! The nicest boat in the Tampa Bay area. If you are in the market for a daysail... View Details

    View 10 Photos and Details Contact Seller
    $20,650
    VIEW DETAILS
  • 1981 Cape Dory 28

    1981 Cape Dory 28

    $20,500
    Merritt Island, FL
    • Merritt Island, FL
    • Sailboat
    • 28' / 0'
    • 1981 / Used
    • $20,500

    - Stock #158900 - Wonderful 2 Owner vessel. A Classic that has been maintained with integrity and hard work. A must see! If you are in the market for a sloop, look no further t... View Details

    View 10 Photos and Details Contact Seller
    $20,500
    VIEW DETAILS
  • 1980 Pearson 32

    1980 Pearson 32

    $20,000
    Daytona Beach, FL
    • Daytona Beach, FL
    • Sailboat
    • 32' / 0'
    • 1980 / Used
    • $20,000

    - Stock #221708 - Very nice and well maintained 1980 Pearson 32! Ready to sail! If you are in the market for a cruiser, look no further than this 1980 Pearson 32, just reduced... View Details

    View 10 Photos and Details Contact Seller
    $20,000
    VIEW DETAILS
  • 1989 Pearson P31-2

    1989 Pearson P31-2

    $20,000
    Daytona Beach, FL
    • Daytona Beach, FL
    • Sailboat
    • 31' / 0'
    • 1989 / Used
    • $20,000

    - Stock #200985 - This is a well maintained boat. Winged Keel, 18 Gal Fuel Tank, new upholstery and foam, 2 Cylinder Yanmar. If you are in the market for a sloop, look no furth... View Details

    View 10 Photos and Details Contact Seller
    $20,000
    VIEW DETAILS
  • 1981 Schock New York 36

    1981 Schock New York 36

    $19,995
    Titusville, FL
    • Titusville, FL
    • Sailboat
    • 36' / 0'
    • 1981 / Used
    • $19,995

    - Stock #215415 - A high performance cruising yacht, the Schock 36 New York was designed by architect Bill Cook and was built by the W.D. Schock Corp. If you are in the market... View Details

    View 10 Photos and Details Contact Seller
    $19,995
    VIEW DETAILS
  • 1990 Com Pac 33

    1990 Com Pac 33

    $19,990
    Naples, FL
    • Naples, FL
    • Sailboat
    • 33' / 0'
    • 1990 / Used
    • $19,990

    - Stock #187481 - Good condition Com-Pac 33 repowered with Mitsubishi 26hp diesel If you are in the market for a sloop, look no further than this 1990 Com-Pac 33, just reduced... View Details

    View 10 Photos and Details Contact Seller
    $19,990
    VIEW DETAILS
  • 1979 Hardin 45 Ketch

    1979 Hardin 45 Ketch

    $19,900
    Placida, FL
    • Placida, FL
    • Sailboat
    • 45' / 0'
    • 1979 / Used
    • $19,900

    - Stock #140881 - 1979 HARDIN 45 KETCH SAILBOAT SHE HAS BEEN ON SOME ADVENTURES LEHMAN DIESEL If you are in the market for a ketch, look no further than this 1979 Hardin 45 Ket... View Details

    View 10 Photos and Details Contact Seller
    $19,900
    VIEW DETAILS
  • 1970 Columbia 36

    1970 Columbia 36

    $19,750
    Indiantown, FL
    • Indiantown, FL
    • Sailboat
    • 36' / 0'
    • 1970 / Used
    • $19,750

    - Stock #220943 - A classic sailboat with many updates. If you are in the market for a cruiser, look no further than this 1970 Columbia 36, just reduced to $19,750 (offers enco... View Details

    View 10 Photos and Details Contact Seller
    $19,750
    VIEW DETAILS
  • 1988 Watkins 33 Seawolf

    1988 Watkins 33 Seawolf

    $19,750
    Palmetto, FL
    • Palmetto, FL
    • Sailboat
    • 33' / 0'
    • 1988 / Used
    • $19,750

    - Stock #188108 - Excellent Condition, Fully Rigged for Blue Water, Come and See! Low Hours on Yanmar If you are in the market for a sloop, look no further than this 1988 Watki... View Details

    View 10 Photos and Details Contact Seller
    $19,750
    VIEW DETAILS
  • 1979 Irwin 39 Citation

    1979 Irwin 39 Citation

    $19,500
    Palmetto, FL
    • Palmetto, FL
    • Sailboat
    • 39' / 0'
    • 1979 / Used
    • $19,500

    - Stock #220490 - Make an Offer! New Bottom! Low Hours! Needs work to finish..do that and you'll have a great cruiser! If you are in the market for a sloop, look no further tha... View Details

    View 10 Photos and Details Contact Seller
    $19,500
    VIEW DETAILS
Showing 64 to 84 of 104 boats found.
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Sailboats harness wind power for propulsion, offering an eco-friendly and serene boating experience. They come in various types, including sloops, ketches, and catamarans, each with distinct sail configurations. Sizes range from small dinghies to large yachts equipped for ocean crossings. Sailboats are popular for recreational cruising, racing, and liveaboard lifestyles. They require knowledge of wind patterns, navigation, and sail handling, providing an engaging experience for enthusiasts.

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